ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate | 80348-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
• 英文别名: 2-carboethoxy-3,5,5-trimethyl-2-cyclohexenone；Ethyl 2,4,4-trimethyl-6-oxocyclohex-1-ene-1-carboxylate；ethyl 2,4,4-trimethyl-6-oxocyclohexene-1-carboxylate
• CAS: 80348-45-4
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: PNTFDQIRZYXUOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 sodium ethanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以31%的产率得到ethyl 2,2,4-trimethyl-6-oxo-1-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Transition-Metal-Mediated Exo-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions

  摘要：

  2-Cobaloxime-(E)-1,3-pentadienyl complexes (cobaloxime = pyridine(dimethylglyoxime)(2)cobalt(III)) react with a variety of cyclohexenones in [4 + 2] cycloaddition reactions. These cycloaddition reactions produce octalones with cis ring junctions through exo transition states. The octalones are removed from the cobalt via demetalation reactions that replace the cobalt with a hydrogen and provide pyr(dmg)(2)CoMe, which can be recycled into the synthesis of the starting dienyl complex.

  DOI：

  10.1021/jo962076c

文献信息

• Palladium-Catalyzed Intramolecular Oxidative Alkylation of 4-Pentenyl ?-Dicarbonyl Compounds
  作者：Cong Liu、Xiang Wang、Tao Pei、Ross A. Widenhoefer

  DOI：10.1002/chem.200400460

  日期：2004.12.17

  to good yield as the exclusive cyclized product. Deuterium-labeling experiments provided information regarding the mechanism of the palladium-catalyzed oxidative alkylation of 4-pentenyl beta-dicarbonyl compounds.

  8-壬烯-2,4-二酮与催化量的[PdCl2（CH3CN）2]（2; 5摩尔％）和化学计量的CuCl2（2.5当量）在室温下反应3小时导致氧化烷基化并以80％的分离产率形成2-乙酰基-3-甲基-2-环己烯酮。4-戊烯基β-二酮的氧化烷基化可耐受多个末端酰基，并在4-戊烯基链的C1和C3碳原子处取代。同样，在4-戊烯基链的C1，C2或C3碳原子处具有双键解构的4-戊烯基β-酮酯环化形成2-羰基烷氧基-2-环己烯酮，以中等至良好的收率作为排他的环化产物。氘标记实验提供了有关4-戊烯基β-二羰基化合物的钯催化氧化烷基化机理的信息。
• Andreeva, L. N.; Perlova, T. G.; Negrebetskii, V. V., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 9, p. 1800 - 1801
  作者：Andreeva, L. N.、Perlova, T. G.、Negrebetskii, V. V.、Dymova, S. F.、Koroleva, T. I.、et al.

  DOI：——

  日期：——
• ANDREEVA L. N.; PERLOVA T. G.; NEGREBETSKIJ V. V.; DYMOVA S. F.; KOROLEVA+, ZH. ORGAN. XIMII, 1981, 17, HO 9, 2017-2018
  作者：ANDREEVA L. N.、 PERLOVA T. G.、 NEGREBETSKIJ V. V.、 DYMOVA S. F.、 KOROLEVA+

  DOI：——

  日期：——
• Transition-Metal-Mediated <i>Exo</i>-Selective Diels−Alder Reactions for the Preparation of Octalones with Unusual Stereochemistries. Reactions of 2-Cobaloxime-Substituted 1,3-Dienes with Cyclohexenones in Thermal and Lewis Acid-Catalyzed [4 + 2] Cycloadditions
  作者：B. Matthew Richardson、Mark E. Welker

  DOI：10.1021/jo962076c

  日期：1997.3.1

  2-Cobaloxime-(E)-1,3-pentadienyl complexes (cobaloxime = pyridine(dimethylglyoxime)(2)cobalt(III)) react with a variety of cyclohexenones in [4 + 2] cycloaddition reactions. These cycloaddition reactions produce octalones with cis ring junctions through exo transition states. The octalones are removed from the cobalt via demetalation reactions that replace the cobalt with a hydrogen and provide pyr(dmg)(2)CoMe, which can be recycled into the synthesis of the starting dienyl complex.